title: Investigating the initial steps in the biosynthesis of cyanobacterial sunscreen scytonemin.
abstract: The cyanobacterial natural product scytonemin (1) functions as a sunscreen, absorbing harmful UV-A radiation. Using information from a recently identified gene cluster, we propose a biosynthetic route to this pigment. We also report the characterization of two enzymes, NpR1275 and NpR1276, which are involved in the initial stages of this pathway. A regioselective acyloin reaction between indole-3-pyruvic acid (4) and p-hydroxyphenylpyruvic acid (5) is a key step in assembling the carbon framework of a proposed monomeric scytonemin precursor (2).
authors.affiliation: Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, Boston, Massachusetts 02115, USA.
authors.forename: Emily P
authors.initials: EP
authors.lastname: Balskus
authors.forename: Christopher T
authors.initials: CT
authors.lastname: Walsh
mesh_terms: D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D000458:Cyanobacteria / Q000737:chemistry* / Q000378:metabolism*; D007211:Indoles / Q000737:chemistry* / Q000378:metabolism*; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry* / Q000378:metabolism*; D013473:Sunscreening Agents / Q000737:chemistry* / Q000378:metabolism*
chemical_list: D007211:Indoles; D010636:Phenols; D013473:Sunscreening Agents; C083368:scytonemin